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温度

0 °C

To a solution of (2-chloro-1,3-thiazol-5-yl)methanol (0.30 g, 2.00 mmol) in anhydrous CH2Cl2 (20.0 mL) was added thionyl chloride (0.50 g, 4.20 mmol) followed by triethylamine (0.40 g, 4.00 mmol) at 0° C. After stirring at 0° C. for one hour and ambient temperature for one hour, the reaction mixture was diluted with CH2Cl2 (50.0 mL) and extracted with water (2×20 mL). The organic phase was dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo to dryness. The residue was dissolved in methyl-ethyl ketone (10.0 mL) followed by the additions of spiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-2′(1′H)-one (0.36 g, 2.00 mmol) and cesium carbonate (1.95 g, 6.00 mmol). The reaction mixture was heated at 70° C. overnight, cooled, filtered and the filtrate was concentrated in vacuo to dryness. The residue was subjected to column chromatography to yield the title compound (0.032 g, 3.4%) as a colorless solid: mp 195-198° C.; 1H NMR (300 MHz, DMSO-d6) δ 7.81 (s, 1H), 7.39-6.93 (m, 5H), 6.66 (s, 1H), 6.15-6.12 (m, 1H), 5.89 (d, 2H), 5.10 (s, 2H), 4.70 (dd, 2H); MS (ES+) m/z 413.1 (M+1).

1. extractionextracted with water (2×20 mL)
2. dry with materialThe organic phase was dried over Na2SO4
3. filtrationfiltered
4. concentrationThe filtrate was concentrated in vacuo to dryness
5. dissolutionThe residue was dissolved in methyl-ethyl ketone (10.0 mL)
6. temperatureThe reaction mixture was heated at 70° C. overnight
7. temperaturecooled
8. filtrationfiltered
9. concentrationthe filtrate was concentrated in vacuo to dryness